wherein
Q is hydrogen; C1-C22alkyl; —OH; —OR7; —NR7R8; or —N═R9;
R1 is hydrogen; C1-C22alkyl; —OR7, —SR7; —NR7R8; C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; C1-C12heteroalkyl, C2-C11heteroaralkyl; C8-C10aryl; or C1-C9heteroaryl;
R4 is cyano; COR7, COOR7; CONR7%; SO2(C6-C12)aryl; C2-C12alk-1-enyl; C3-C12cycloalk-1-enyl; C2-C12alk-1-inyl; C2-C12heteroalkyl; C3-C5heterocycloalkyl; C1-C10aryl; or C1-C9heteroaryl;
R5 is —COR7; —COOR7; —OR7; —SR7, —NHR7, —NR7R8; C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; C1-C12alkylphenyl; C1-C12alkoxy-C6-C10aryl; C1-C12heteroalkyl; C2-C11 heteroaralkyl; C3-C12cycloheteroalkyl; C5-C10aryl; C1-C12alkoxy-C6-C10aryl; or C1-C9heteroaryl;
R6 is hydrogen; C1-C22alkyl; C1-C22alkoxy; or COR7;
R7 and R8 independently from each other are hydrogen; C1-C22alkyl; C2-12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; —(CH2)tCOOH; C7-C12aralkyl; C1-C12heteroalkyl; C2-C11heteroaralkyl; C6-C10aryl; C1-C9heteroaryl; Si—R10R11R12; Si(OR10)(OR11)(OR12); SiR10(OR11)(OR12); SiR10R11(OR12); —(CH2)u˜O—(CH2)v—SiR10R11R12; or a radical X-Sil;
t, u and v, independently from each other are a number from 1 to 5;
R9 is a (C1-C6)alkylidene radical;
R10, R11, R12 independently form each other are C1-C22alkyl;
X is a linker;
Sil is a silane-, oligosiloxane- or polysiloxane radical;
R1 and R2, R1 and Q, R1 and R6, R1 and T, R2 and R3, R2 and R4, R2 and R6, R2 and Q, R4 and R6, R4 and T, R6 and Q, T and Q, each independently, are linked together, so that 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocylic rings are formed, wherein each of them, independently from each other, may be condensed with an aromatic or heteroaromatic ring, and/or more N—, O and/or S-heterocyclic rings, and each N atom in a N-heterocyclic ring may be substituted by C1-C22alkyl;
n is a number from 1 to 4; wherein at least one of the radicals R1, R6 or Q is different from hydrogen;
if n=1
T is —COR5; —CN; C6-C10aryl; —NHR5; or —SO2—(C6-C12)aryl;
R2 and R3 independently from each other are C1-C22alkyl; hydroxy-C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl, C3-C12cycloalkenyl; C7-C12aralkyl; C1-C12heteroalkyl; C3-C12cycloheteroalkyl; C6-C10aryl; C1-C9heteroaryl; or a radical of formula

p is a number from 5 to 100
q is a number from 1 to 5;
s is a number from 0 to 4;
if n=2
R2 and R3 are each C1-C5alkylene; and simultaneously T is defined as for n=1; or
T is a bivalent radical of formula —NR7—V—NR7—, wherein
V is phenylene; or C1-C5alkylene;
R7 is hydrogen; or C1-C5alkyl; and R2 and R3 simultaneously are defined as for n=1;
if n=3
one of R2, R3 or T is a trivalent radical;
if n=4
one of R2, R3 or T is a tetravalent radical;
for protecting of human hair and skin against the damaging effect of UV radiation.

Halogen ist chloro, bromo, fluoro or iodo, preferably chloro.

Alkyl, cycloalkyl, alkenyl, alkylidene or cycloalkenyl may be straight chained or branched, monocyclic or polycyclic.

C1-C12heteroaryl is an unsaturated or aromatic radical having 4n+2 conjugated π-electrons, for example 2-thienyl, 2-furyl, 2-pyridyl, 2-thiazolyl, 2-oxazolyl, 2-imidazolyl, isothiazolyl, tri-azolyl, tetrazolyl or another ring system from thiophene-, furan-, pyridine, thiazol, oxazol, imidazol, isothiazol, triazol, pyridine- and benzene rings, which are unsubstituted or substituted by 1 to 6 ethyl, methyl, ethylene and/or methylene, like benzotriazolyl, bei N-heterocycles optionally in the form of their N-oxides.

C2-C16heteroaralkyl is for example C1-C8alkyl substituted with C1-C8heteroaryl.

More preferred is the use of the compounds of formula (I), wherein
Q is —OH; —OR6; or —NR7R8;
T is —COR5—CN; or —SO2—(C6-C12)aryl;
R1 is hydrogen; —OR7, —SR7; —NR7R8; C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-C10aryl;
R2 and R3 independently from each other are C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-C10aryl;
R4 is cyano; —COR5, —COOR7; —CONR7R8; —SO2(C6-C12)aryl; —C1-C22alkylcarbonylamino-C6-C10aryl; or C6-C10aryl;
R5 is —COR7; —COOR7; —CONR1R8, —OR7, —SR7, —NR7R8, C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; C6-C10aryl; or C1-C12alkoxy-C6-C10aryl;
R6, R7 and R8 independently from each other are hydrogen; C1-C22alkyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-C10aryl; or
R1 and R2, R1 and Q, R1 and R4, R1 and R6, R2 and R3, R3 and Q, R6 and Q, T and Q are linked together pairwise, so that 1, 2, 3 or 4 carbocyclic or N-, O- and/or S-heterocyclic rings are formed, wherein each of them, independently from each other may be condensed with an aromatic or heteroaromatic ring, and/or more N, O and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by C1-C22alkyl.

Even more preferred is the use of the compounds of formula (I), wherein
R1 is hydrogen; —S—C1-C22alkyl; or R1 and R2, or R1 and R4 together with the linking nitrogen atom form an alkylene radical which my be interrupted by one or more —O— and/or —NR7— or may be condensed with an aromatic ring; and
R7 is C1-C22alkyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-C10aryl.

Most preferred is the use of the compounds of formula (1), wherein

R1 is hydrogen.

Furthermore, the use of compounds formula (I) is preferred, wherein
R2 and R3 independently from each other are C1-C5alkyl; phenyl-C1-C3alkyl; hydroxy-C1-C12alkyl; or R2 and R3, or R2 and R4, or R2 and Q together with the linking nitrogen atom form an alkylene radical which my be interrupted by one or more —O— and/or —NR7— or may be condensed with an aromatic ring; and
R7 is C1-C22alkyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-C10aryl;

And most preferably the use of the compounds of formula (I), wherein
R2 and R3 independently from each other are C1-C5alkyl; or R2 and R3 together with the linking nitrogen atom form a C2-C4alkylene radical which may be interrupted by —O— or —NR7; and
R7 is hydrogen; or C1-C5alkyl.

Preferred is also the use of compounds of formula (I), wherein
R4 is —COR5; phenyl, which is optionally substituted by C1-C5alkyl; —CN; or —SO2—(C6-C10)aryl; or
R4 and T together with a bivalent C3-C7alkylene radical which my be interrupted by one or more —O— and/or —NR7— form a carbocyclic ring which may be condensed with an aromatic ring; and
R7 is hydrogen; or C1-C6alkyl.

Furthermore the use of compounds of formula (I) is preferred, wherein

R4 is —CN; or COR5;

R5 is C1-C12alkyl; or C1-C12alkoxy; or
R4 and T together with the bivalent radical of the formula

wherein
U1 and U3 independently from each other are a radical of formula —CHR7; —NHR7—; or —O—;
U2 is —CH2; or —CO—; or the direct bond;
R7 is hydrogen; or C1-C12alkyl; form an aromatic ring.

Most preferred is the use of compounds of formula (I), wherein

T and R4 together with the bivalent radicals selected from

form a heterocyclic ring.

Furthermore, the use of compounds of formula (I) is preferred, wherein
R6 is hydrogen; C1-C5alkyl; C1-C5alkoxy; —O—(C6-C10aryl); or
R6 and Q together with a bivalent C3-C7alkylene radical which may be interrupted by one or more —O— and/or —NR7— or may be condensed with an aromatic ring, form a heterocyclic ring; and
R7 is hydrogen; or C1C12alkyl; and most preferably wherein
R6 is hydrogen.

Furthermore, the use of compounds ofse according to any of formula (1) is preferred, wherein
T is —CN; —COR5; or —SO2-phenyl;
R5 is C1-C5alkyl; C1-C5alkoxy; or NR7R8;
R7 and R8 independently from each other are hydrogen; or C1-C5alkyl; or
T and Q together with the bivalent C3-C7alkylene radical which may be interrupted by one or more —O— and/or —NR7— or may be condensed with an aromatic ring, form a heterocyclic ring; and most preferably the use of compounds of formula (I), wherein
T is —CN; or —COR5; and
R5 is C1-C5alkyl; or C1-C6alkoxy.

Furthermore, the use of compounds of formula (I) is preferred, wherein.
Q is hydroxy; C1-C5alkoxy; or —NR7R8; and
R7 and R8 independently from each other are hydrogen; C1-C5alkyl; or phenyl, which may be substituted by one or more C1-C5alkyl or C1-C5alkoxy groups; and most preferably, wherein
Q is hydroxy.

Furthermore, the use of compounds of formula

is preferred, wherein
U4, U5, U6, U7 and U8 independently of each other are —CHR5—; —CO—; —NR7—; —CS—; or —O—;
R5 is hydrogen; or C1-C5alkyl; and
R1, R2, R3, R6, R7 and Q are defined as in formula (1).

Furthermore, the use of compounds of formula

is preferred, wherein
R5 is hydrogen; or C1-C5alkyl; and
R3, R4, and T are defined as in formula (1); more preferably, wherein
R3 is C1-C22alkyl; C6-C10aryl; or C7-C12aralkyl; and most preferably, wherein
R3 is C6-C10aryl.

Furthermore, the use of compounds of formula (I) is preferred, wherein at least one of the radicals R1, R6 or Q is different from hydrogen.

Preferred is also the use of compounds of formula (I), wherein
Q is hydrogen; or C1-C22alkyl;
T is —COR6; —CN; or —SO2—(C6-C12)aryl;
R1 is hydrogen; or C1-C22alkyl;
R2 and R3 independently from each other are C1-C22alkyl;
R4 is CN; COR5; CONH2; or SO2(C6-C12)aryl,
R5 is —OR7; —SR7, —NHR7, —NR7R8; C1-C22alkyl; C7-C12aralkyl;
R7 and R8 independently from each other are hydrogen; C1-C22alkyl; —(CH2)m—Si—R10R11R12; Si(OR10)(OR11)(OR12); SiR10(OR11)(OR12); SiR10R11(OR12), or a radical X-Sil;
R9 is a (C1-C6)alkylidene radical;
R10, R11, R12 independently form each other are C1-C22alkyl;
X is a linker;
Sil is a silane-, oligosiloxane- or polysiloxane radical;
R1 and R2, R1 and Q, R1 and R6, R1 and T, R2 and R3, R2 and R4, R2 and R6, R2 and Q, R4 and R6, R4 and T, R6 and Q, T and Q, each independently, are linked together, so that 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings are formed, wherein each of them, independently from each other, may be condensed with an aromatic or heteroaromatic ring, and/or more N-, O- and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by C1-C22alkyl;
n is a number from 1 to 4; and
m is a number for 0 to 4; wherein at least one of the radicals R1, R6 or Q is different from hydrogen;

Preferred is the use of compounds of formula (I), wherein

R1, R6 and Q, independently from each other are hydrogen; or C1-C22alkyl, wherein at least one of R1, R6 and Q is different from hydrogen; and most preferred the use of compounds of formula (1), wherein
R1, R6 and Q, independently from each other are hydrogen; or C1-C5alkyl, wherein at least one of R1, R6 and Q is different from hydrogen.

Preferred is also the use according of compounds of formula (I), wherein
T and R4 independently from each other are —COR6; —CN; or —SO2—(C6-C12)aryl; and
R5 is —OR7; —NR7R5; C1-C22alkyl; C7-C12aralkyl;
R7 and R8 independently from each other are hydrogen; C1-C22alkyl; —(CH2)m—Si—R10R11R12; and
R10, R11, and R12 independently from each other are C1-C22alkyl.

Most preferred is the use of compounds of formula (I), wherein T and R4 independently from each other are —CN; SO2C6H5;

or a radical of formula

wherein
R7 and R8, independently from each other are C1-C12alkyl; or a radical of formula —SiR10R11R12; and
R10, R11 and R12 are C1-C5alkyl.

Furthermore the present invention relates to the use of monomeric and polymeric compounds having the structural element of formula

wherein at least one of the asterix-marked radicals are joint with the monomeric or polymeric radical; and
R1, R2, R4 and R6 are defined as in formula (I).

Examples of merocyanine derivatives used in the present invention are listed in Table 1:

In J. Heterocyclic Chem., 27, 1990, 1143-1151 aminoacrylic acid esters or aminoacrylnitriles are reacted with ethoxymethylenecyanoacetates in ethanol to the corresponding compounds used in the present invention.

The compounds of the formula (I) according to the present invention are particularly suitable as UV filters, i.e. for protecting ultraviolet-sensitive organic materials, in particular the skin and hair of humans and animals, from the harmful effects of UV radiation. These compounds are therefore suitable as sunscreens in cosmetic, pharmaceutical and veterinary medical preparations. These compounds can be used both in dissolved form and in the micronized state.

The UV absorbers according to the present invention can be used either in the dissolved state (soluble organic filters, solubelized organic filters) or in the micronised state (nano-scalar organic filters, particulate organic filters, UV-absorber pigments).

Any known process suitable for the preparation of microparticles can be used for the preparation of the micronised UV absorbers, for example wet-milling, wet-kneading, spray-drying from a suitable solvent, by the expansion according to the RESS process (Rapid Expansion of Supercritical Solutions) by reprecipitation from suitable solvents.

The micronised UV absorbers so obtained usually have an average particle size from 0.02 to 2, preferably from 0.03 to 1.5, and more especially from 0.05 to 1.0 micrometer.

A further object of the present invention is a UV absorber dispersion, comprising

(a) a micronised UV absorber of formula (I), each of them having a particle size from 0.02 to 2 μm, and
(b) a suitable dispersing agent.

The cosmetic formulations or pharmaceutical compositions according to the present invention may additionally contain one or more than one further conventional UV filter.

The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments. In addition to the above-mentioned UV filters, the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.

As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or microemulsions) the preparations contain, for example, from 0.1 to 30% by weight, preferably from 0.1 to 15% by weight and especially from 0.5 to 10% by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60% by weight, especially from 5 to 50% by weight and preferably from 10 to 35% by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30% by weight, especially from 1 to 30% by weight und preferably from 4 to 20% by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90% by weight, especially from 30 to 90% by weight, based on the total weight of the composition, of water, and from 0 to 88.9% by weight, especially from 1 to 50% by weight, of further cosmetically acceptable adjuvants.

The compounds of formula (I) may also be used as an anti-wrinkle perception modifier (see Example 29). This is a further object of the present invention.

Preferably, the following combinations comprising UV absorbers are of special interest:

The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments. In addition to the above mentioned UV filters, the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.

As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or microemulsions) the preparations contain, for example, from 0.1 to 30% by weight, preferably from 0.1 to 15% by weight and especially from 0.5 to 10% by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60% by weight, especially from 5 to 50% by weight and preferably from 10 to 35% by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30% by weight, especially from 1 to 30% by weight und preferably from 4 to 20% by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90% by weight, especially from 30 to 90% by weight, based on the total weight of the composition, of water, and from 0 to 88.9% by weight, especially from 1 to 50% by weight, of further cosmetically acceptable adjuvants.

The final formulations listed may exist in a wide variety of presentation forms, for example:
in the form of liquid preparations as a W/O, O/W, O/W/O, W/O/W or PIT emulsion and all kinds of microemulsions,
in the form of a gel,
in the form of an oil, a cream, milk or lotion,
in the form of a powder, a lacquer, a tablet or make-up,
in the form of a stick,
In the form of a spray (spray with propellent gas or pump-action spray) or an aerosol,
in the form of a foam, or
in the form of a paste.

Of special importance as cosmetic preparations for the skin are light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or tropicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams. Of particular interest are sun protection creams, sun protection lotions, sun protection milk and sun protection preparations in the form of a spray.

Of special importance as cosmetic preparations for the hair are the above-mentioned preparations for hair treatment, especially hair-washing preparations in the form of shampoos, hair conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-straightening preparations, liquid hair-setting preparations, hair foams and hairsprays. Of special interest are hair-washing preparations in the form of shampoos.

A shampoo has, for example, the following composition: from 0.01 to 5% by weight of a UV absorber according to the invention, 12.0% by weight of sodium laureth-2-sulfate, 4.0% by weight of cocamidopropyl betaine, 3.0% by weight of sodium chloride, and water ad 100%.

The cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight.

PREPARATION EXAMPLES
Example 1
Preparation of the Compound of Formula

A mixture of 8.58 g of dehydroacetic acid with 7.63 g of N,N-Dimethylformamid-dimethyl-acetate in 100 ml of tert.-butylmethylether is stirred for 8 hours at room temperature. Then the product is filtered off, washed with minor amounts of tert.-butylmethylether and dried in vacuum at 40° C.

The yield is nearly quantitative. Fp: 159-161° C.

Example 2
Preparation of Compound of Formula

A mixture of 1 g of 1-Ethoxycarbonyl-1 cyano-2-(N-dimethylaminomethylen)amino-4-di-methylaminobutadiene (prepared according to Chem. Heterocycl. Compd. (Engl. Transl.), 24, 8, 1988, 918) with 0.43 g of p-toluidine in 10 ml of dimethylformamide is boiled for 1 hour. The solvent is evaporated, the residue is ground in ether, filtered and dried in vacuum at 40° C. yielding 0.75 g of colorless crystals. Fp: 210-216° C.

The reaction mixture is stirred for 4 h at 3° C. and finally for 16 h at room temperature.

The raw product is filtered off and washed with diethylether and finally 4 times with 10 ml methanol.

After drying in vacuo at 60° C. 2.70 g of the product of formula (I) are obtained as bright-orange crystals.

λmax=396 nm.

Example 4
Preparation of the Compound: of Formula

A mixture of 1.16 g of 1-Ethoxycarbonyl-1-cyano-2-(N-dimethylaminomethylen)amino-4-dimethylaminobutadiene (prepared according to Chem. Heterocycl. Compd. (Engl. Transl.), 24, 8, 1988, 918) with 0.47 g of aniline in 11 ml of acetic acid is boiled for 1 hour. After cooling to room temperature the product is filtered off, recrystallized from toluene/ethyl acetate (1:1) yielding yellow crystals which were dried in vacuum at 40° C. The yield is 25%. λmax=363 nm.

Part A and part B are heated separately to 75° C. Part A is poured into part B under continuous stirring. Immediately after the emulsification, Cyclopentasiloxane and PEG-12 Dimethicone from part D are incorporated into the mixture. Afterwards the mixture is homogenized with an Ultra Turrax at 11000 rpm for 30 sec. After cooling down to 65° C. Sodium Acrylates Copolymer (and) Paraffinium Liquidum (and) PPG-1 Trideceth-6 are incorporated. Part C is added at a temperature <50° C. At a temperature≦35° C. Tocopheryl Acetate is incorporated and subsequently the pH is adjusted with Water (and) Citric Acid. At room temperature part E is added.

Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75° C. Part B is prepared and heated to 75° C. At this temperature part B is poured into part A under progressive stirring speed. Then the mixture is homogenized (30 sec., 15000 rpm). At a temperature c 55° C. the ingredients of part C are incorporated. The mixture is cooled down under moderate stirring, then the pH is checked and adjusted with triethanolamine.

Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75° C. Part B is prepared and heated to 75° C. At this temperature, part B is poured into part A under progressive stirring speed. Below 65° C. the ingredients of part D are added separately. After cooling down under moderate stirring to 55° C. part C is added. The pH is then checked and adjusted with sodium hydroxide. The mixture is homogenized for 30 sec at 16000 rpm.

Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75° C. Part C is prepared and heated to 75° C. Part C is poured into the part A under moderate stirring. Immediately after the emulsification part B is added, then neutralized with a part of the triethanolamine. The mixture is homogenized for 30 sec. After cooling down under moderate stirring Cyclopentasiloxane (and) Dimethiconol are added. Below 35° C. the pH is checked and adjusted with triethanolamine.

Part A and part B are heated up to 80° C. Part A is blended into part B under stirring and homogenized with an UltraTurrax at 11000 rpm for 30 sec. Part C is heated to 60° C. and added slowly to the emulsion. After cooling down to 40° C. part D is incorporated at room temperature and part E is added.

Part A and B are heated to 75° C. Part A is added into part B under continuous stirring and homogenized with 11000 rpm for 1 minute. After cooling down to 50° C. part C is added under continuous stirring. After cooling further down to 30° C. part D is added. Afterwards the pH is adjusted between 6.00-6.50.

Part A and B are heated separately to 75° C. After adding part B into part A the mixture is homogenized with Ultra Turrax for one minute at 11000 rpm. After cooling down to 50° C. part C is added. Afterwards the mixture is homogenized for one minute at 16000 rpm. At a temperature <40° C. part D is added. At room temperature the pH-value is adjusted with part E between 6.00 and 6.50.

Part A and B are heated separately up to 75° C., part C is heated to 60° C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11000 rpm and part C is incorporated. After cooling down to 40° C. part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.

Part A and B are heated separately up to 75° C., part C is heated to 60° C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11000 rpm and part C is incorporated. After cooling down to 40° C. part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.

Part A and part B are heated separately to 75° C. Part B is added into part A under continuous stirring and afterwards homogenized with Ultra Turrax for 30 sec at 11000 rpm. After cooling down to 60° C. part C is added. At 40° C. part C is added and homogenized for 15 sec at 11000 rpm. At room temperature the pH-value is adjusted with part E.

Part A and B are heated separately to 75° C.; part C to 60° C. Part B is poured into part A under stirring. After one-minute of homogenization at 11000 rpm part C is added to the mixture of A/B. After cooling down to 40° C. part D is incorporated. At room temperature the pH value is adjusted with part E between 6.3 and 7.0. Finally part F is added.

Part A and part B are heated separately to 75° C. Part A is poured into part B under stirring. Immediately after the emulsification, part C is added to the mixture and homogenized with an Ultra Turrax at 11000 rpm for 30 sec. After cooling down to 65° C. Sodium Acrylates Copolymer (and) Mineral Oil (and) PPG-1 Trideceth-6 At 50° C. is added slowly to the UV absorber dispersion. At about 35-30° C. part F is incorporated. The pH is adjusted with part G between 5.5 and 6.5.

Part A and part B are heated separately up to 80° C. Part A is poured into part B while stirring and homogenized with an Ultra Turrax by 11000 rpm for 30 sec. After cooling down to 60° C. part C is incorporated. At 40° C. part D is added slowly under continuous stirring. The pH is adjusted with part E between 6.50-7.00.

Part A and part B are heated separately up to 80° C., part C is heated to 50° C. Part B is poured into part A and homogenized with an Ultra Turrax for 1 minute at 11000 rpm. After cooling down to 50° C. part C is added under continuous stirring. At 40° C. part D is incorporated and homogenized again for 10 sec. at 11000 rpm. The pH is adjusted with part E.

Part A and part B are heated separately up to 75° C., part C is heated to 60° C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11000 rpm and part C is incorporated. After cooling down to 40° C. part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.

Part A and part B are heated separately to 80° C. Part A is poured into part B under continuous stirring. Afterwards the mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 min. After cooling down to 60° C. part C is incorporated. At 40° C. part D is added and the mixture homogenized for a short time again. At 35° C. part E is added and at room temperature Fragrance is added. Finally the pH is adjusted with Sodium Hydroxide.

Part A and part B are heated separately up to 80° C. Part B is poured into part A under moderate stirring. The mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 minute. After cooling down to 70° C. part C is added under stirring. After cooling further down to 50° C. part D is incorporated very slowly. At 40° C. part E is added. At room temperature the pH is adjusted with part F to 7.00 and part G is added.

Part A and part B are heated separately up to 80° C. Part B is poured into part A under moderate stirring. The mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 minute. After cooling down to 70° C. add part C is added under stirring. After cooling further down to 50° C. part D is incorporated very slowly. At 40° C. part E is added. At room temperature the pH is adjusted with part F to 7.00 and part G is added.

Part A and part B are heated separately up to 75° C. Part B is poured into part A under progressive stirring speed. At a temperature <65° C. the ingredients of part D are added separately. After cooling down to 55° C. under moderate stirring part C is added. At a temperature <35° C. the pH is checked and adjusted with Sodium Hydroxide and homogenized with an Ultra Turrax for 30 sec. at 11000 rpm. Part F is added at room temperature.

Part A is heated separately to 80° C. under gentle stirring. Part B is added to part A and homogenized for one minute at 11000 rpm. After cooling down to 30° C. part C is added under continuous stirring.

Part A and part B are heated separately to 80° C. Part A is poured into part B, whilst stirring continuously. Afterwards the mixture is homogenized with an Ultra Turrax at 11000 rpm for 20 sec. The mixture is cooled to 60° C. and part C is added. At a temperature below 30° C., part D is added and the pH value is adjusted with sodium hydroxide to between 6.5 and 7.0. Finally, fragrance is added.

Part A and part B are heated separately to 75° C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11000 rpm for 15 sec. The mixture is cooled to 60° C. and part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec./11000 rpm) and further cooled, with moderate stirring. At room temperature, the pH is adjusted with sodium hydroxide solution to between 5.5 and 6.0. Finally, fragrance is added.

Heat part A and part B separately to 75° C. Pour part A into part B, whilst stirring continuously. Immediately after emulsification, incorporate in the mixture SF 1202 and SF 1288 from part D. Afterwards homogenise with an Ultra Turrax at 11000 rpm for 30 sec. Allow to cool to 65° C. and incorporate SALCARE® SC91. At a temperature below 50° C., add part C. At 35° C. or below, incorporate vitamin E acetate and subsequently adjust the pH with citric acid. At room temperature, add part E.

Part A and part B are heated separately to 75° C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11000 rpm for 15 sec. The mixture is cooled to 60° C., and part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec./11000 rpm). After further cooling, with moderate stirring, the pH is adjusted with sodium hydroxide at room temperature. A solution between pH 5.50 and 6.00 is obtained. Finally, fragrance is added.

Part A and part B are heated separately to 75° C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11000 rpm for 15 sec. After cooling 60° C., part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec./11000 rpm). After further cooling, with moderate stirring, the pH is adjusted at room temperature with sodium hydroxide solution to between 5.50 and 6.00. Finally, fragrance is added.

Part A and part B are heated separately to 75° C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11000 rpm for 15 sec. After cooling to 60° C., part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec./11000 rpm). After further cooling, with moderate stirring, the pH is adjusted at room temperature with sodium hydroxide. A solution between pH 5.50 and 6.00 is obtained. Finally, fragrance is added.

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